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Annonaceousacetogenins compounds and preparation method thereof

A kind of technology of annua lactone and compound, which is applied in the field of tetrahydrofuran-containing annua lactone compound and its preparation, and can solve problems such as unsatisfactory performance.

Inactive Publication Date: 2008-04-30
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the existing tetrahydrofuran-containing annonaceous lactone compounds (compounds shown in formula I) have antitumor activity, their performance is not satisfactory enough, and there is still room for improvement

Method used

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  • Annonaceousacetogenins compounds and preparation method thereof
  • Annonaceousacetogenins compounds and preparation method thereof
  • Annonaceousacetogenins compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] Where: MOM is CH 2 OCH 3 (the same below)

[0024] Dissolve 0.32mmol of compound 4 in freshly distilled tetrahydrofuran solution, place it in a low-temperature tank at -78°C and stir for 10 to 15 minutes, then add 0.15mL of hexane solution with a concentration of 2.5Mn-BuLi dropwise, after the dropwise addition is complete, continue Stir for 30 minutes; then drop the tetrahydrofuran solution of compound 5 into the system, continue the reaction for 1 to 2 hours, quench the reaction with saturated ammonium chloride at 0°C, extract with ethyl acetate, and dry over anhydrous sodium sulfate , concentrated, and column chromatography gave 143 mg of the product (compound 3), with a yield of 55%.

[0025]

[0026] 0.29 mmol of compound 3 was dissolved in a mixture consisting of 0.5-10 ml of methanol, tetrahydrofuran and 6N hydrochloric acid, wherein the volume ratio of 6N hydrochloric acid, tetrahydrofuran and methanol was 1:1:2. Stir at room temperature for ab...

Embodiment 2

[0032] The structural formula is The ditetrahydrofuryne compound and the structural formula are The chiral epoxy compound reaction, operation is with embodiment 1, can obtain following object (compound 6):

[0033]

[0034] Structural characterization data of compound 6:

[0035] 1 HNMR (CDCl 3 , 400MHz) δ: 7.18(q, J=1.5Hz, 1H), 5.09(qq, J=6.8, 1.5Hz, 1H), 4.06(m, 1H), 3.97(m, 1H), 3.85(m, 1H ), 3.84(m, 2H), 3.59(m, 1H), 3.38(m, 2H), 2.53(m, 1H), 2.40(ddt, J=15.2, 8.5, 1.8Hz), 2.05(m, 1H) , 1.96(m, 2H), 1.70-1.45(m, 23H), 0.88(t, J=7.0Hz, 3H);

[0036] 13 CNMR (CDCl 3 , 100MHz): δ174.6, 151.9, 131.2, 83.5, 82.6, 81.5, 80.8, 78.2, 74.5, 73.6, 71.7, 70.0, 33.5, 28.8, 28.3, 19.0, 14.1.

Embodiment 3

[0038] The structural formula is The ditetrahydrofuryne compound and the structural formula are or The chiral epoxy compound reaction, operation is with implementing 1, can obtain following object (compound 7 and compound 8):

[0039]

[0040] Structural characterization data of compound 7:

[0041] 1 H-NMR (CDCl 3 , 400MHz) δ 7.18(q, J=1.5Hz, 1H), 5.09(qq, J=6.8, 1.5Hz, 1H), 4.06(m, 1H), 3.97(m, 1H), 3.85(m, 1H) , 3.84(m, 2H), 3.59(m, 1H), 3.38(m, 2H), 2.53(m, 1H), 2.40(ddt, J=15.2, 8.5, 1.8Hz), 2.05(m, 1H), 1.96(m, 2H), 1.70-1.45(m, 19H), 0.88(t, J=7.0Hz, 3H);

[0042] 13 CNMR (CDCl 3, 100MHz): δ174.6, 151.9, 131.2, 83.5, 82.6, 81.5, 80.8, 78.2, 74.5, 73.6, 71.7, 70.0, 43.6, 38.1, 33.5, 28.8, 28.3, 23.0, 19.0, 14.1.

[0043]

[0044] Structural characterization data of compound 8:

[0045] 1 H-NMR (CDCl 3 , 400MHz) δ 7.18(q, J=1.5Hz, 1H), 5.09(qq, J=6.8, 1.5Hz, 1H), 4.06(m, 1H), 3.97(m, 1H), 3.85(m, 1H) , 3.84(m, 2H), 3.59(m, 1H), 3.38(m, 2H), 2.53(m, 1...

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Abstract

The invention relates to annonaceous acetogenin compound including tetrahydrofuran and the preparation method thereof. The structure of the annonaceous acetogenin compound is shown as the formula A or the formula B. The method to prepare the annonaceous acetogenin compound comprises the main steps that: under the condition of the existence of lithium alkyl, the ring opening coupling reaction is operated through chiral double tetrahydrofuran alkyne compound with a blocking group and chiral epoxy lactone compound with a blocking group to obtain intermediate compound, the deprotection reaction and the electronation reaction are operated in sequence to the intermediate compound to obtain an object. Compared with the prior annonaceous acetogenin compound including the tetrahydrofuran, the antineoplastic activity of the annonaceous acetogenin compound including the tetrahydrofuran prepared by the invention is obviously improved. In the formula A and the formula B, m is 2 to 10, n is 5 to 8.

Description

technical field [0001] The invention relates to an annonaceous lactone compound and a preparation method thereof, in particular to an annonaceous lactone compound containing tetrahydrofuran and a preparation method thereof. Background technique [0002] Natural anemone lactones are contained in Annonaceae plants, and they have become the focus of scientists' attention due to their good anti-tumor activity and anti-multidrug resistance. [0003] Tetrahydrofuran-containing annonaceous lactones are an important class of annonaceous lactones (J. Nat. Prod. 2005, 68, 194-197). A kind of annonaceous lactone compound containing tetrahydrofuran is reported, and its structure is as shown in formula I: [0004] [0005] In formula I, a is 2-10, b is 5-8 [0006] Although the existing tetrahydrofuran-containing annona lactone compounds (compounds represented by formula I) have antitumor activity, their performance is not satisfactory, and there is still room for improvement. Con...

Claims

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Application Information

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IPC IPC(8): C07D307/58A61P35/00
Inventor 曾步兵李彩梅郭淑春王涛嵇雯浩
Owner EAST CHINA UNIV OF SCI & TECH
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